Some advice on breaking in a virgin bottom

[Jablackanese]

Hello! I am about 9" x 5x5" there's a guy I hooked up with last year, who I find very sexy. Young ex-HS wrestler frat boy. We didn't have anal/oral sex, mostly he sucked on my nipples, licked my neck, although I did finger and rim his virgin ass and jacked off onto it. He is straight, as in he'd never been with a guy or had his ass played with. I have big hands, but my fingers are long and slender, however he said my finger really hurt, even as I went slowly and used one finger at a time.

He's been emailing me about taking his virginity, and I like the idea, but I'm thinking "geez, if you can't even take a finger w/o pain and warm-up rimming, how could you actually bottom??" I'm by no means a monster thick cock, but I am worried that we'll hook up and it'll just be a "no-go."

I've bottomed three times, and each time the cock was bigger than the last one. The biggest one def took a min, but I wasn't screaming in pain. So I feel like my personal experience might not help in this case. Plus, this guy is smaller than me (height, smaller hands, mouth, etc), so his hole might just be a lot smaller/tighter..? idk. I'm posting a pic of his delicious butt (and my dick because what the heck) so you'll understand why I'm so eager to make it work :biggrin1:

Thanks in advance for any advice you can give me.

 

[deleted786880]

lots of lube, and go really slow with that shlong, make sure he knows its ok to tell you that it hurts, and watch his body language to see if he likes it or it hurts

 

[Infernal]

Patience, lots of lube and pay attention to his body language. Don't race to shove it in and bang away. Take your time and let him get use to the new sensations of having his ass played with. It might not happen the first time, but that's always a good reason to try again.

 

[Jablackanese]

thank you! ... I spent a lot of time rimming to warm him up and help him relax, but I didn't use lube for my finger. I'll def have on a condom, can anyone recommend a good lube? I have KY, but is there anything out there that's even better to use w/ a tight virgin bottom?

 

[macho8]

people always say let him sit on it... this is not right... it usually mean that when he's squatting down this is ass is tighten up... get him doggy or on his back

 

[Infernal]

While not a favorite of mine, try something that's silicone based. It usually stays slick for a long time and you won't have to keep stopping to put more on. I don't think KY is good for anything other than medical stuff. Drys out too fast, gets sticky, etc.

Lots of finger play to get him loosened up, and worked up. Sitting on it the first time might be hard for him, but it's different for everyone. Worked well for me the first few times I did it. I like a guy flat on his stomach, but on his back might be good so you can watch his face for signs of pain. Let him tell you how much and how fast.

 

[Jablackanese]

really appreciating all the advice guys, truly

 

[thkdck4u]

Speaking from a guy who has never fucked a guy, but have broken in a few virgin females, some of whom were very reluctant, I can offer this.

Don't be in a hurry. In fact, don't even set a time limit. I can remember 2 girls that finally ended up loving anal, and were dead set against it in the beginning. They were open to external licking and touching only. Eventually, that became extended rimming sessions that stemmed from oral, and the occasional finger.

Eventually, there was interest in "trying" it with no promises. So, first...enema. "Fleet" is good. I explained that the idea is to relax, and when she was going to become that relaxed, there was potential for a mess. I leave that up to them to "prepare" before I get there. I'm not into that. Some are, I guess.

So, the beginners, in my experience, follow the same course: the idea is to help them relax and trust you. Lots of foreplay, massaging, then rimming. In some one case, she just laid on her stomach with her legs spread and watched a movie, while I rimmed her for about an hour. They get to the point where they want something inserted. So small, finger, larger finger, maybe two. Lots of lube (I liked one called 'Wet'). Communication and compliments help. It's not tough to get them relaxed enough to take two fingers. After that, an anal toy helps. A small buttplug, or dildo. Plus that really helps them get into the mood that they are going to have things up their ass.

You'll know when they are relaxed enough. There is no resistance at all, just complete relaxation. Then you have to tell them that the first inch or two is the easy part, it's the secondary "sphincter" that seems to have a mind of it's own as to whether or not it's open for business that you have to really be patient with.

Mentally, tell them, it's like someone is just knocking at the door. You don't want to force the door open, or barge your way in, you want to just "knock on the door", and let them relax and open the door every step of the way right from the beginning, all the way up to your balls.

Second, tell them to do the pushing. You just provide the hard cock, let them take it at their pace. Third, tell them when they are pushing against you, to think about pushing "out" like they are taking a shit. This relaxes the ass. It's the same as taking a giant shit, except something is going in rather than going out.

Hope this helps.

 

[rbkwp]

Perhaps
dont let him slip away too readily
ie
crying 'i cant take it' could mean
'i really want it', lets just try a different method / position

plus we dont want him to have an experience with a curious LPSG Str poking around now do we
inexperience can be frightening?? ha

No advice, cept take it easy, and be gentle .. sounds like you are!
and if at first you dont succeed etc ha just go out for dinner, and try try again
waaahooooooo enjoy yourselves Matey ..

 

[D_Aurifice_Stupher]

To the OP, geez your dick should be named Captain Hook. You could put that in my back door any time, looks like it would hit all the right spots. And his butt is to die for, looks feminine, especially with that G-String and a load of cum all over it. Sexy.

I've not had a real one, but do dildos all the time. Lots of lube and go slowly to get in the first time. For me it takes five or six attempts to get through the initial pain of entry. After that it's all good. ;-)

Want someone to do me, just have not found anyone willing in this boring state. :frown1:

 

[deleted6173571]

That's sweet <3 Best lube for me is love! So make him feel desired, make that foreplay so hot he looses control/consciousness, find his triggers (sucking on my ears drives me wild for instance) build from there, and don't stop when the fucking starts! I'm a lot more relaxed when I know my partner is crazy about me. I'm a lot more open when I can feel his pleasure, hear his grunts, and when the guy is verbal. I'm personally a sucker for a muscle flexer during the action (you don't have to be ripped, just bigger, and have attitude), makes me so wet. Last trick for me is to push lots of lube in with your dick, just once slowly, then pull out, then fuck with even more lube.